I haven’t been in a while, but unless things have significantly changed, commuting from Carroll county or Grenada or Winona sounds crazy to me. The nice parts of Greenwood used to be pretty nice (at least for a small town) and safe and nicer than what was available in any place within commuting distance. Nothing in Carroll county or Grenada or Winona would make me want to sign up for a commute into greenwood unless you just want to be in the country and find some nice land.
The one thing I might worry about is an exit plan, depending on how old you are and how healthy you are. I'm assuming if you are in Greenwood, you have pretty limited options for healthcare when it comes to specialists and I would assume their hospital can't be great. I guess people drive to Jackson? Or Memphis? I think I'd be hesitant to be somewhere long term without decent healthcare options in 20-30 minutes. But make good money to cap off the career before moving back somewhere I had roots? Definitely would be a potential option.
Carrollton is an easy 19 mile, four-lane, no traffic drive to Greenwood. Winona would be 30 minutes to Greenwood, but puts you on 55 (easier drive to Jxn/Memphis), plus an hour drive to Starkvegas.
Long time Mayor, Carolyn McAdams, with the help of Viking/Fred Carl (and one other man), has kept Greenwood from turning into a poophole, like every other Delta town with the exception of Cleveland. Fred sold Viking and I don't know how much runway Carolyn has left, when she's gone Greenwood will devolve quickly.
If healthcare is an issue, don't move to Greenwood, other than a routine check up/sinus infection means a trip to Jxn, Memphis or Oxford (which has become the go to for many in the area). The hospital is still open, but just barely, you wouldn't want to have to stay there in any of the few beds left (Grenada hospital is decent though). I have standing orders, if hurt on the farm, get me to Jxn.
Bottom line, if you take the job, be wary of buying a house in Greenwood, if determined to live in Greenwood, try to rent first. There are some beautiful homes there, but I look at a house as an investment more than anything else.
If you long for the days off Mayberry, Carrollton is exactly that. If you want a little more convenience, Winona is the place, but buying a house anywhere in the area is risky.